directing Hill wanted to be a writer since he was young and dreamed of joining the writing teams of The Simpsons, Saturday Night Live, and The Larry Sanders Show. At one point, Hill was writing a screenplay with close friend and I Heart Huckabees co-star Jason Schwartzman. He wrote Pure Imagination, a comedy for Sony about a man who develops an imaginary friend after a traumatic experience. Filming was expected to begin in 2008 but it has been in development since then. Hill was a co-producer on the movie Brüno and did some writing for Sacha Baron Cohen, who "taught him how to become a better writer". Hill co-wrote the treatment for the 2012 film 21 Jump Street with screenwriter Michael Bacall. Hill directed the music videos for the Sara Bareilles song "Gonna Get Over You" from her 2010 album Kaleidoscope Heart, the Danny Brown song "Ain't it Funny" from his 2016 album Atrocity Exhibition, Travis Scott's song "Wake Up" from his 2018 album Astroworld, and the Vampire Weekend song "Sunflower" from their 2019 album Father of the Bride. Hill wrote and directed (but did not appear in) the 2018 coming-of-age film Mid90s. Hill directed (and appears in) Stutz, a 2022 Netflix documentary. Personal life In July 2011, Hill appeared at the 2011 ESPN ESPY Awards having lost a significant amount of weight; he later said he had done so to seek more serious roles. He explained that he consulted with a trainer and a nutritionist, and had changed his diet to mainly sushi. He is also known to train in Brazilian jiu jitsu and described it as "humbling". In October 2019, he and Gianna Santos were engaged; they ended the engagement in October 2020. Hill says: "TM [transcendental meditation] along with surfing, I'd say that those two things have changed my happiness level and my ability to cope with stress, anxiety and depression… [they've] really helped." In 2016, Architectural Digest reported that Hill bought a four-bedroom loft in the Noho neighborhood of Manhattan in New York City. In October 2021, Hill asked fans to stop making comments about his physical appearance, stating: "I know you mean well but I kindly ask that you not comment on my body, good or bad I want to politely let you know it's not helpful and doesn't feel good. Much respect." In November 2022, he filed a petition to legally drop "Feldstein" from